Electrophilic alkylation of arenes with 5-bromopyrimidine en route to 4-aryl-5-alkynylpyrimidines

A new synthetic protocol for preparation of medicinally important 4-aryl-5-alkynylpyrimidines is described. The featured approach involves a sequence of chemo- and regioselective Brønsted acid-catalyzed electrophilic alkylation of arenes with 5-bromopyrimidine, followed by oxidative re-aromatization...

Descripción completa

Detalles Bibliográficos
Autores principales: Shcherbakov, Stanislav S., Magometov, Artyom Yu., Shcherbakova, Viktoriia Yu., Aksenov, Alexander V., Domenyuk, Dmitriy A., Zelensky, Vladimir A., Rubin, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9050372/
https://www.ncbi.nlm.nih.gov/pubmed/35498620
http://dx.doi.org/10.1039/d0ra01335h
_version_ 1784696349483073536
author Shcherbakov, Stanislav S.
Magometov, Artyom Yu.
Shcherbakova, Viktoriia Yu.
Aksenov, Alexander V.
Domenyuk, Dmitriy A.
Zelensky, Vladimir A.
Rubin, Michael
author_facet Shcherbakov, Stanislav S.
Magometov, Artyom Yu.
Shcherbakova, Viktoriia Yu.
Aksenov, Alexander V.
Domenyuk, Dmitriy A.
Zelensky, Vladimir A.
Rubin, Michael
author_sort Shcherbakov, Stanislav S.
collection PubMed
description A new synthetic protocol for preparation of medicinally important 4-aryl-5-alkynylpyrimidines is described. The featured approach involves a sequence of chemo- and regioselective Brønsted acid-catalyzed electrophilic alkylation of arenes with 5-bromopyrimidine, followed by oxidative re-aromatization of the formed dihydropyrimidine ring. Finally, palladium-catalyzed Sonogashira cross-coupling reaction provided an end-game strategy.
format Online
Article
Text
id pubmed-9050372
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-90503722022-04-29 Electrophilic alkylation of arenes with 5-bromopyrimidine en route to 4-aryl-5-alkynylpyrimidines Shcherbakov, Stanislav S. Magometov, Artyom Yu. Shcherbakova, Viktoriia Yu. Aksenov, Alexander V. Domenyuk, Dmitriy A. Zelensky, Vladimir A. Rubin, Michael RSC Adv Chemistry A new synthetic protocol for preparation of medicinally important 4-aryl-5-alkynylpyrimidines is described. The featured approach involves a sequence of chemo- and regioselective Brønsted acid-catalyzed electrophilic alkylation of arenes with 5-bromopyrimidine, followed by oxidative re-aromatization of the formed dihydropyrimidine ring. Finally, palladium-catalyzed Sonogashira cross-coupling reaction provided an end-game strategy. The Royal Society of Chemistry 2020-03-10 /pmc/articles/PMC9050372/ /pubmed/35498620 http://dx.doi.org/10.1039/d0ra01335h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Shcherbakov, Stanislav S.
Magometov, Artyom Yu.
Shcherbakova, Viktoriia Yu.
Aksenov, Alexander V.
Domenyuk, Dmitriy A.
Zelensky, Vladimir A.
Rubin, Michael
Electrophilic alkylation of arenes with 5-bromopyrimidine en route to 4-aryl-5-alkynylpyrimidines
title Electrophilic alkylation of arenes with 5-bromopyrimidine en route to 4-aryl-5-alkynylpyrimidines
title_full Electrophilic alkylation of arenes with 5-bromopyrimidine en route to 4-aryl-5-alkynylpyrimidines
title_fullStr Electrophilic alkylation of arenes with 5-bromopyrimidine en route to 4-aryl-5-alkynylpyrimidines
title_full_unstemmed Electrophilic alkylation of arenes with 5-bromopyrimidine en route to 4-aryl-5-alkynylpyrimidines
title_short Electrophilic alkylation of arenes with 5-bromopyrimidine en route to 4-aryl-5-alkynylpyrimidines
title_sort electrophilic alkylation of arenes with 5-bromopyrimidine en route to 4-aryl-5-alkynylpyrimidines
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9050372/
https://www.ncbi.nlm.nih.gov/pubmed/35498620
http://dx.doi.org/10.1039/d0ra01335h
work_keys_str_mv AT shcherbakovstanislavs electrophilicalkylationofareneswith5bromopyrimidineenrouteto4aryl5alkynylpyrimidines
AT magometovartyomyu electrophilicalkylationofareneswith5bromopyrimidineenrouteto4aryl5alkynylpyrimidines
AT shcherbakovaviktoriiayu electrophilicalkylationofareneswith5bromopyrimidineenrouteto4aryl5alkynylpyrimidines
AT aksenovalexanderv electrophilicalkylationofareneswith5bromopyrimidineenrouteto4aryl5alkynylpyrimidines
AT domenyukdmitriya electrophilicalkylationofareneswith5bromopyrimidineenrouteto4aryl5alkynylpyrimidines
AT zelenskyvladimira electrophilicalkylationofareneswith5bromopyrimidineenrouteto4aryl5alkynylpyrimidines
AT rubinmichael electrophilicalkylationofareneswith5bromopyrimidineenrouteto4aryl5alkynylpyrimidines

Ejemplares similares